Dibasic-acid salts and method of making same



is vaporized, mixed with air or an oxygen Patented July 23, 1929.-

i U ED STATES.

PATENT OFFICE.

JOSEPH 111px JAMES, or PITTSBURGH, riEnnsYLvANIA.

mBAsrc-Aom SALTS AND METHOD OF'MAKING SAME.

N'o Drawing. Application filed April 4, 1922, Serial No. 549,567, Renewe dDecember 5, 1928.

dibasic acid salts or soaps and the method of aldehyde fatty acids.

In the said process, the liquid hydrocarbon containing gas in regulated proportions, near the theoretical combining proportion or preferably in excess thereof, and the hot mixture is passed, with or without the addition of a dilutlng gas, such as steam, through a relatively thin layer or through successive relatively thin layers of catalytic material under a regulated temperature, preferably below 500 C. The catalysts'employed are preferably complex oxides 'or compounds of metals havin a varying valence, such for example, as the Inc oxides of molybdenum. The prod nets of this partial-combustion or partialoxidation process arethen condensed, giving amixture of partial-oxidation products, ranging from alcohols through, aldehydes to aldehyde fatty acids. The process may be varied to produce more or less of the alde hyde fatty acids and of aldehydes.

As the liquid hydrocarbon is usually a certain fraction or cut of mineral oil, such as petroleum containing hydrocarbons of verying molecular'weight, the condensed product contains aldehyde fatty acids of varying mo- I 4 v brown in color and has an aldehydic odor, and

as the chlorine causes the oxidation, the color changes finally becoming lighter, and in many lecular weights in admixture.

her 5, 1919, I'have describeda certain method of making soaps and metallic salts of the aldehyde' fatty acid thus produced. I have, however, experienced much difiicult-y 1n obtaining soaps or compounds by the methods of thelast named applications, of light color and free from aldehydic odor. My present invention isde signed to overcome this difficulty, and it consists in oxidizing these aldehyde fatty acids, preferably by using one of the halogens to make a lighter colored product, free or substantially free from the aldehydic odors. The soaps may be made either by the method described in the above copending applications, or by any ordlnarymethod of soap manufacture, and the oxidation may be carried on either during or after such soap formation. The acids are thus preferably taking oxidized to dibasic acids, thus in many cases obtaining soaps of a white color and free from aldehydic odors.

While many chemical methods may be used for oxidizing the aldehyde acids into dibasic acids, I will now set forth a preferred process 3 I therefor.

I take the condensation product formed by my vapor-phase partial-oxidation process, above referred to, and form soaps, preferably sodium or potassium soaps, from the aldehyde fatty acids contained in the mixture.

To the heated water solution of the sodium or potassium soaps of these acids, I add sufficient caustic soda or caustic potash or other carbonates, to keep the bath alkaline during the oxidation. That is, I add the caustic, preferably gradually, in sutficient amount to have enough caustic present to react with the acid groups formed by theox'idation of the aldehyde groupsin the aldehyde acid soaps and keep a slight excess, by successive addithe solution (keeping the caustic in slight eX- cess) and the course of the reaction may be easily followed by noting the color changes place. The original solution of the aldehyde fatty acid soaps is usually dark cases,'entirely white; and the resulting soaps have little or none of the objectionable aldehydic odor.

' In this method, as above outlined, when the oxidation is complete, soaps are produced of the dibasic acids of varying molecular weight corresponding to the aldehyde acids in the original mixture. These soaps are usually of sufficient purity to be salted out,

after concentrating the solution by evaporation, if necessary.

If in any case it IS desired to further purify the dibasic acids, they may, after the oxidation step, be liberatedfrom the sodium or potassium soaps by mineral acids, and then purified by any of the well known methods of purifying organic compounds, such as by vacuum distillation. p

. cient method is afforded for producing dibasic acids. I

Instead of using a water solution of the soaps, I may use another solvent which is not appreciably attacked by the oxidizing agent, such as alcohol. In this case, I may use either the soaps or the free acids in carrying out the step of oxidation. I may also dissolve the original condensation product of the vaporphase oxidation in a solvent, such as alcohol, not appreciably attacked by the oxidizing agent, and then introduce the oxidizing agent, preferably the hydrochlorite solution. In this case, in addition to oxidizing the aliphatic fatty acids, I will oxidize the aldehydes to true fatty acids and the aldehye alcohols to hydroxy-acids. Then the saponifying step may be carried out, giving a mixture of different soaps.

Many variations may be-made in the reagents employed, and the steps may be varied without departing from my invention, as defined in the broader claims.

My new step of oxidizing these aldehyde fatty acids may also be applied to the oxygenated acids obtained in the cotton seed oil industry and other industries, such oxygenated acids probably containing aldehyde acids in all or in most cases. Attempts have been made to utilize such oxygenated acids by reducing them, but such attempts have failed, so far as I am aware. My step is the opposite of this, since it oxidizes these acids to dibasic acids. Any of the methods herein described may be applied to such oxygenated acids, as well as to those obtained by my preferred method of manufacture from mineral oils.

I make no claim herein to the mixtureo-f dibasic acids or the method of producing them, as claims thereon are nresent'in my acids and forming chemical salts of said dibasic acids.

2. In the treatment of liquid oxygenated organic acids derived from mineral oil, the steps consisting of oxidizing them into dibasic acids and forming chemical salts of said dibasic acids.

3. The process consisting in oxidizing oxygenated acids derived from mineral oil into dibasic acids and then converting a part of the dibasic acids into soap.

4. In the treatment of a mixture of oxygenated organic acids derived from mineral oil, the steps consistingof oxidizing them into dibasic acids and forming chemical salts of said dibasic'acids. i

5. As a new article of manufacture, a soap containing the salts of aliphatic dibasic acids of different molecular weights.

6. As a new article. of manufacture, a soap containing the ammonium salts of aliphatic dibasic acids of different molecular weights.

7. As a new article of manufacture, the mixture of salts of dibasic acids produced by oxidizing oxygenated organic acids obtained by gaseous partial oxidation of aliphatic hydrocarbons.

8. As a new article of manufacture, the mixture of salts of dibasic acids produced by oxidizing the oxygenated organic acids present in the'product obtained by gaseous partial oxidation of aliphatic hydrocarbons, the mixture also containing other salts produced by said further oxidation of said partial oxidation product. p

9. As a new article of manufacture, the mixture of salts of dibasic acids of different molecular weights produced by oxidizing the oxygenated organic acids present in the product obtained by gaseous partial oxidation of aliphatic hydrocarbons, the mixture also containing other salts produced by said further oxidation of said partial oxidation product.

In testimony whereof I have hereunto set my hand.

JOSEPH HIDY JAMES. 

